Sodium Hydroxide → N-(Toluene-4sulfonyl)-N-methyl-L-phenylalanyl-D,L-phenylalanine

HRID 411262Notes

Reaction equation

HRID 411262 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([S:7]([N:10]([CH3:22])[C@H:11]([C:19]([OH:21])=O)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C([O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH2:29])C.[OH-].[Na+]>C(O)C>[C:1]1([CH3:23])[CH:2]=[CH:3][C:4]([S:7]([N:10]([CH3:22])[C@H:11]([C:19]([NH:29][CH:28]([C:27]([OH:37])=[O:26])[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:21])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76506Phenylalanine ethyl esterHCID 12069251N-(toluene-4-sulfonyl)-N-methylphenylalanine

Product 1

HCID 12069253N-(Toluene-4sulfonyl)-N-methyl-L-phenylalanyl-D,L-phenylalanine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Methyl-L-phenylalanine (500 mg, 2.79 mmol) was dissolved in 1N NaOH (6 mL). Dioxane (9 mL)) was added, followed by p-toluenesulfonyl chloride (532 mg, 2.79 mmol) and the mixture was vigorously stirred for 1 hr. The volatiles were removed in vacuo and the residue was dissolved in water (30 mL) and washed with Et2O (2×30 mL) before making acidic with 1N HCl. The mixture was extracted with CHCl3 (3×30 mL) and the extracts were evaporated in vacuo to give N-(toluene-4-sulfonyl)-N-methylphenylalanine as a solid (424 mg, 45%). N-(Toluene-4-sulfonyl)-N-methylphenylalanine was coupled to L-phenylalanine ethyl ester using the procedure described in Method 3 (400 mg, 62%). The title compound was prepared via hydrolysis of the ethyl ester using NaOH in ethanol. Proton and carbon NMR analyis indicated a mixture of diastereomers.

Workup

  1. additiona mixture of diastereomers

Sources & evidence

ORD record
ord-228bf1ed31914e93a6e213ddcdcc1054
Source dataset
uspto-grants-2003_05
Patent number
US06559127B1

Reaction notes

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